SF2575

naturalproductmech:mibig-95308e3c7c MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

Structure

Standard InChIKey	WYRYRHFKSQKGHJ-FRKPEAEDSA-N
SMILES	C/C=C(\C)/C(=O)OC1C(OC(CC1O)C2=C(C3=C(C=C2)C(C4CC5C(C(=O)C(=C(C5(C(=O)C4=C3O)OC)O)C(=O)N)OC(=O)C6=CC=CC=C6O)(C)OC)O)C
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:54702959

Filing pathway

Polyketides — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is pks, saccharide, from MIBiG.

Producer organisms 1

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Streptomyces sp. SF2575 NCBITaxon:746675	BGC_CHARACTERIZED	mibig:BGC0000269	DOI:10.7164/antibiotics.45.320

Occurrences 1

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

Taxon	Source	Reference
Streptomyces NCBITaxon:1883	LOTUS	DOI:10.7164/ANTIBIOTICS.45.325

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000269	Streptomyces sp. SF2575 NCBITaxon:746675	CLUSTER_DEMONSTRATED	genbank:GQ409537.1

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Streptomyces sp. SF2575 SsfM2-catalyzed C6 O-methylation in SF2575 biosynthesis.

Subject	Predicate	Object	Notes	Evidence
SsfM2 O-methylation substrate	is O-methylated by	SsfM2 O-methyltransferase	MITE represents SsfM2 as the O-methyltransferase for an SF2575 tetracycline intermediate; an exact local record is absent for the submitted substrate structure.	DOI:10.1002/anie.201205426 https://mite.bioinformatics.nl/repository/MITE0000021 https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk https://www.uniprot.org/uniprotkb/D6MSW0 https://www.ncbi.nlm.nih.gov/protein/ADE34498.1 reference DOI:10.1002/anie.201205426 evidence type PRIMARY_EXPERIMENT snippet inactivation of ssfM2 led to the isolation of three different desmethyl compounds notes Wang et al. inactivated ssfM2 in a Streptomyces lividans K4-114 heterologous host carrying the SF2575 ssf cluster, isolated C6-desmethyl SF2575-pathway products, restored SF2575 production by complementation with ssfM2, and assigned SsfM2 as the C6 O-methyltransferase. reference https://mite.bioinformatics.nl/repository/MITE0000021 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000021 is active, links SsfM2 to UniProtKB:D6MSW0, GenPept ADE34498.1 and MIBiG BGC0000269, and represents a knock-out-supported O-methylation reaction in the SF2575 biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk evidence type DATABASE_ASSERTION snippet MITE0000021: Methylation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000269.5 places ssfM2/ADE34498.1 inside the active Streptomyces sp. SF2575 biosynthetic gene cluster as a biosynthetic-additional locus with a 100% identity MITE0000021 methylation annotation. reference https://www.uniprot.org/uniprotkb/D6MSW0 evidence type DATABASE_ASSERTION snippet GN Name=ssfM2 retrieved on 2026-10-02 notes Current UniProtKB:D6MSW0 resolves as a 331 aa Streptomyces sp. SF2575 SsfM2 entry and cross-references EMBL GQ409537 protein ADE34498.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE34498.1 evidence type DATABASE_ASSERTION snippet O-methyltransferase retrieved on 2026-10-02 notes NCBI Protein ADE34498.1 is the 331 aa Streptomyces sp. SF2575 SsfM2 O-methyltransferase encoded by ssfM2 at complement(GQ409537.1:19848..20843).
SsfM2 O-methyltransferase	forms	SsfM2 O-methylated SF2575 intermediate	The MITE SsfM2 reaction methylates an oxygen atom of an SF2575-pathway tetracycline intermediate.	DOI:10.1002/anie.201205426 https://mite.bioinformatics.nl/repository/MITE0000021 https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk https://www.uniprot.org/uniprotkb/D6MSW0 https://www.ncbi.nlm.nih.gov/protein/ADE34498.1 reference DOI:10.1002/anie.201205426 evidence type PRIMARY_EXPERIMENT snippet inactivation of ssfM2 led to the isolation of three different desmethyl compounds notes Wang et al. inactivated ssfM2 in a Streptomyces lividans K4-114 heterologous host carrying the SF2575 ssf cluster, isolated C6-desmethyl SF2575-pathway products, restored SF2575 production by complementation with ssfM2, and assigned SsfM2 as the C6 O-methyltransferase. reference https://mite.bioinformatics.nl/repository/MITE0000021 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000021 is active, links SsfM2 to UniProtKB:D6MSW0, GenPept ADE34498.1 and MIBiG BGC0000269, and represents a knock-out-supported O-methylation reaction in the SF2575 biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk evidence type DATABASE_ASSERTION snippet MITE0000021: Methylation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000269.5 places ssfM2/ADE34498.1 inside the active Streptomyces sp. SF2575 biosynthetic gene cluster as a biosynthetic-additional locus with a 100% identity MITE0000021 methylation annotation. reference https://www.uniprot.org/uniprotkb/D6MSW0 evidence type DATABASE_ASSERTION snippet GN Name=ssfM2 retrieved on 2026-10-02 notes Current UniProtKB:D6MSW0 resolves as a 331 aa Streptomyces sp. SF2575 SsfM2 entry and cross-references EMBL GQ409537 protein ADE34498.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE34498.1 evidence type DATABASE_ASSERTION snippet O-methyltransferase retrieved on 2026-10-02 notes NCBI Protein ADE34498.1 is the 331 aa Streptomyces sp. SF2575 SsfM2 O-methyltransferase encoded by ssfM2 at complement(GQ409537.1:19848..20843).

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Causal graph — biosynthesis 5 nodes, 4 edges

Streptomyces sp. SF2575 SsfM4-catalyzed SAM-dependent C-methylation toward 6-methylpretetramide in SF2575 biosynthesis.

Subject	Predicate	Object	Notes	Evidence
SsfM4 C-methylation substrate	is C-methylated by	SsfM4 C-methyltransferase	MITE represents SsfM4 as the C-methyltransferase for an SF2575-pathway tetracycline intermediate; an exact local record or ChEBI grounding is absent for the submitted substrate structure.	DOI:10.1002/anie.201205426 DOI:10.1021/ja907852c https://mite.bioinformatics.nl/repository/MITE0000022 https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk https://www.uniprot.org/uniprotkb/D6MSU6 https://www.ncbi.nlm.nih.gov/protein/ADE34484.1 reference DOI:10.1002/anie.201205426 evidence type PRIMARY_EXPERIMENT snippet SsfM4 was identified to catalyze C6 C-methylation by heterologous reconstitution in CH999. notes Wang et al. inactivated ssfM4 in a Streptomyces lividans K4-114 heterologous host carrying the SF2575 ssf cluster, observed products lacking C6 methylation, and concluded that the C6 methyl transfer occurs early to generate 6-methylpretetramide. reference DOI:10.1021/ja907852c evidence type PRIMARY_EXPERIMENT snippet C-6 methylation of 47, which is catalyzed by the OxyF homolog SsfM4. notes Pickens et al. placed ssfM4 in the 40-ORF SF2575 biosynthetic gene cluster and heterologously reconstituted production of the oxidized 6-methylpretetramide product WJ119 after adding ssfL2 to ssfY1Y2M4. reference https://mite.bioinformatics.nl/repository/MITE0000022 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000022 is active, links SsfM4 to UniProtKB:D6MSU6, GenPept ADE34484.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported C-methylation reaction in the SF2575 biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk evidence type DATABASE_ASSERTION snippet MITE0000022: Methylation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000269.5 places ssfM4/ADE34484.1 inside the active Streptomyces sp. SF2575 biosynthetic gene cluster as a biosynthetic-additional locus with a 100% identity MITE0000022 methylation annotation. reference https://www.uniprot.org/uniprotkb/D6MSU6 evidence type DATABASE_ASSERTION snippet GN Name=ssfM4 retrieved on 2026-10-02 notes Current UniProtKB:D6MSU6 resolves as a 343 aa Streptomyces sp. SF2575 SsfM4 entry and cross-references EMBL GQ409537 protein ADE34484.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE34484.1 evidence type DATABASE_ASSERTION snippet C-methyltransferase retrieved on 2026-10-02 notes NCBI Protein ADE34484.1 is the 343 aa Streptomyces sp. SF2575 SsfM4 C-methyltransferase encoded by ssfM4 at GQ409537.1:4053..5084.
S-adenosyl-L-methionine	supplies a methyl group to	SsfM4 C-methyltransferase	MITE lists SAM as an SsfM4 organic cofactor and UniProt annotates D6MSU6 as a SAM-binding methyltransferase-family protein.	https://mite.bioinformatics.nl/repository/MITE0000022 https://www.uniprot.org/uniprotkb/D6MSU6 reference https://mite.bioinformatics.nl/repository/MITE0000022 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000022 is active, links SsfM4 to UniProtKB:D6MSU6, GenPept ADE34484.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported C-methylation reaction in the SF2575 biosynthetic pathway. reference https://www.uniprot.org/uniprotkb/D6MSU6 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes UniProtKB:D6MSU6 contains class I-like SAM-binding methyltransferase family annotations on the current Streptomyces sp. SF2575 SsfM4 entry.
iron-sulfur cluster	serves as cofactor for	SsfM4 C-methyltransferase	MITE lists FeS as an SsfM4 inorganic cofactor without specifying the iron-sulfur cluster geometry.	https://mite.bioinformatics.nl/repository/MITE0000022 reference https://mite.bioinformatics.nl/repository/MITE0000022 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000022 is active, links SsfM4 to UniProtKB:D6MSU6, GenPept ADE34484.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported C-methylation reaction in the SF2575 biosynthetic pathway.
SsfM4 C-methyltransferase	forms	6-methylpretetramide	The MITE reaction product matches the CHEBI:27879 SMILES for 6-methylpretetramide, a locally inventoried ChEBI intermediate that does not have a NaturalProductRecord in this corpus.	DOI:10.1002/anie.201205426 DOI:10.1021/ja907852c https://mite.bioinformatics.nl/repository/MITE0000022 https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk https://www.uniprot.org/uniprotkb/D6MSU6 https://www.ncbi.nlm.nih.gov/protein/ADE34484.1 reference DOI:10.1002/anie.201205426 evidence type PRIMARY_EXPERIMENT snippet SsfM4 was identified to catalyze C6 C-methylation by heterologous reconstitution in CH999. notes Wang et al. inactivated ssfM4 in a Streptomyces lividans K4-114 heterologous host carrying the SF2575 ssf cluster, observed products lacking C6 methylation, and concluded that the C6 methyl transfer occurs early to generate 6-methylpretetramide. reference DOI:10.1021/ja907852c evidence type PRIMARY_EXPERIMENT snippet C-6 methylation of 47, which is catalyzed by the OxyF homolog SsfM4. notes Pickens et al. placed ssfM4 in the 40-ORF SF2575 biosynthetic gene cluster and heterologously reconstituted production of the oxidized 6-methylpretetramide product WJ119 after adding ssfL2 to ssfY1Y2M4. reference https://mite.bioinformatics.nl/repository/MITE0000022 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000022 is active, links SsfM4 to UniProtKB:D6MSU6, GenPept ADE34484.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported C-methylation reaction in the SF2575 biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk evidence type DATABASE_ASSERTION snippet MITE0000022: Methylation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000269.5 places ssfM4/ADE34484.1 inside the active Streptomyces sp. SF2575 biosynthetic gene cluster as a biosynthetic-additional locus with a 100% identity MITE0000022 methylation annotation. reference https://www.uniprot.org/uniprotkb/D6MSU6 evidence type DATABASE_ASSERTION snippet GN Name=ssfM4 retrieved on 2026-10-02 notes Current UniProtKB:D6MSU6 resolves as a 343 aa Streptomyces sp. SF2575 SsfM4 entry and cross-references EMBL GQ409537 protein ADE34484.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE34484.1 evidence type DATABASE_ASSERTION snippet C-methyltransferase retrieved on 2026-10-02 notes NCBI Protein ADE34484.1 is the 343 aa Streptomyces sp. SF2575 SsfM4 C-methyltransferase encoded by ssfM4 at GQ409537.1:4053..5084.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Causal graph — biosynthesis 5 nodes, 4 edges

Streptomyces sp. SF2575 SsfM1-catalyzed SAM-dependent C12a O-methylation in SF2575 biosynthesis.

Subject	Predicate	Object	Notes	Evidence
SsfM1 O-methylation substrate	is O-methylated by	SsfM1 O-methyltransferase	MITE represents SsfM1 as the O-methyltransferase for a C12a hydroxyl group on an SF2575-pathway tetracycline intermediate; exact local records are absent for the submitted substrate and product structures.	DOI:10.1002/anie.201205426 https://mite.bioinformatics.nl/repository/MITE0000023 https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk https://www.uniprot.org/uniprotkb/D6MSX0 https://www.ncbi.nlm.nih.gov/protein/ADE34508.1 reference DOI:10.1002/anie.201205426 evidence type PRIMARY_EXPERIMENT snippet Complementation of ΔssfM1 and ΔssfM2 strains with plasmid-borne copies of ssfM1 and ssfM2, respectively, each restored the production of 2 notes Wang et al. inactivated ssfM1 in a Streptomyces lividans K4-114 heterologous host carrying the SF2575 ssf cluster, isolated the C12a-hydroxyl analog TAN-1518A among three desmethyl products, restored SF2575 production by complementation with ssfM1, and assigned SsfM1 as the C12a O-methyltransferase. reference https://mite.bioinformatics.nl/repository/MITE0000023 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000023 is active, links SsfM1 to UniProtKB:D6MSX0, GenPept ADE34508.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported O-methylation reaction in the SF2575 biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk evidence type DATABASE_ASSERTION snippet MITE0000023: Methylation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000269.5 places ssfM1/ADE34508.1 inside the active Streptomyces sp. SF2575 biosynthetic gene cluster as a biosynthetic-additional locus with a 100% identity MITE0000023 methylation annotation. reference https://www.uniprot.org/uniprotkb/D6MSX0 evidence type DATABASE_ASSERTION snippet GN Name=ssfM1 retrieved on 2026-10-02 notes Current UniProtKB:D6MSX0 resolves as a 332 aa Streptomyces sp. SF2575 SsfM1 entry and cross-references EMBL GQ409537 protein ADE34508.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE34508.1 evidence type DATABASE_ASSERTION snippet O-methyltransferase retrieved on 2026-10-02 notes NCBI Protein ADE34508.1 is the 332 aa Streptomyces sp. SF2575 SsfM1 O-methyltransferase encoded by ssfM1 at complement(GQ409537.1:31776..32774).
S-adenosyl-L-methionine	supplies a methyl group to	SsfM1 O-methyltransferase	MITE lists SAM as an SsfM1 organic cofactor and UniProt annotates D6MSX0 as a SAM-binding methyltransferase-family protein.	https://mite.bioinformatics.nl/repository/MITE0000023 https://www.uniprot.org/uniprotkb/D6MSX0 reference https://mite.bioinformatics.nl/repository/MITE0000023 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000023 is active, links SsfM1 to UniProtKB:D6MSX0, GenPept ADE34508.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported O-methylation reaction in the SF2575 biosynthetic pathway. reference https://www.uniprot.org/uniprotkb/D6MSX0 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes UniProtKB:D6MSX0 contains class I-like SAM-binding methyltransferase family annotations on the current Streptomyces sp. SF2575 SsfM1 entry.
iron-sulfur cluster	serves as cofactor for	SsfM1 O-methyltransferase	MITE lists FeS as an SsfM1 inorganic cofactor without specifying the iron-sulfur cluster geometry.	https://mite.bioinformatics.nl/repository/MITE0000023 reference https://mite.bioinformatics.nl/repository/MITE0000023 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000023 is active, links SsfM1 to UniProtKB:D6MSX0, GenPept ADE34508.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported O-methylation reaction in the SF2575 biosynthetic pathway.
SsfM1 O-methyltransferase	forms	SsfM1 O-methylated SF2575 intermediate	The MITE reaction product methylates an oxygen atom of the submitted SF2575-pathway tetracycline substrate structure.	DOI:10.1002/anie.201205426 https://mite.bioinformatics.nl/repository/MITE0000023 https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk https://www.uniprot.org/uniprotkb/D6MSX0 https://www.ncbi.nlm.nih.gov/protein/ADE34508.1 reference DOI:10.1002/anie.201205426 evidence type PRIMARY_EXPERIMENT snippet Complementation of ΔssfM1 and ΔssfM2 strains with plasmid-borne copies of ssfM1 and ssfM2, respectively, each restored the production of 2 notes Wang et al. inactivated ssfM1 in a Streptomyces lividans K4-114 heterologous host carrying the SF2575 ssf cluster, isolated the C12a-hydroxyl analog TAN-1518A among three desmethyl products, restored SF2575 production by complementation with ssfM1, and assigned SsfM1 as the C12a O-methyltransferase. reference https://mite.bioinformatics.nl/repository/MITE0000023 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000023 is active, links SsfM1 to UniProtKB:D6MSX0, GenPept ADE34508.1 and MIBiG BGC0000269, lists SAM and FeS as cofactors, and represents a knock-out-supported O-methylation reaction in the SF2575 biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000269.5/BGC0000269.gbk evidence type DATABASE_ASSERTION snippet MITE0000023: Methylation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000269.5 places ssfM1/ADE34508.1 inside the active Streptomyces sp. SF2575 biosynthetic gene cluster as a biosynthetic-additional locus with a 100% identity MITE0000023 methylation annotation. reference https://www.uniprot.org/uniprotkb/D6MSX0 evidence type DATABASE_ASSERTION snippet GN Name=ssfM1 retrieved on 2026-10-02 notes Current UniProtKB:D6MSX0 resolves as a 332 aa Streptomyces sp. SF2575 SsfM1 entry and cross-references EMBL GQ409537 protein ADE34508.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE34508.1 evidence type DATABASE_ASSERTION snippet O-methyltransferase retrieved on 2026-10-02 notes NCBI Protein ADE34508.1 is the 332 aa Streptomyces sp. SF2575 SsfM1 O-methyltransferase encoded by ssfM1 at complement(GQ409537.1:31776..32774).

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Explore across X-Mech

AntibioticMech (SF2575) ↗ MediaIngredientMech (naturalproductmech:mibig-95308e3c7c) ↗ TaxonMech: Streptomyces sp. SF2575 (NCBITaxon:746675) ↗ PathwayMech (mibig:BGC0000269) ↗

Provenance

Source concept	Source	Version
BGC0000269	MIBIG	5

This page is generated from data/natural_products/polyketides/sf2575.yaml, which is generated from the committed inventories. Neither is edited by hand.